4303-70-2

Basic information

• Product Name: (E)-9-octadecenamide
• Synonyms: (E)-9-octadecenamide;Elaidoylamide;Einecs 224-316-5;(9E)-9-OctadecenaMide;Elaidic AMide;trans-9-OctadecenaMide
• CAS NO: 4303-70-2
• Molecular Formula: C₁₈H₃₅NO
• Molecular Weight: 281.4766
• EINECS: 224-316-5
• Product Categories: Mixed Fatty Acids;Fatty Acid Derivatives & Lipids;Glycerols;Aliphatics;Aliphatics, Glycerols, Fatty Acid Derivatives & Lipids
• Mol File: 4303-70-2.mol
• Article Data: 6

Chemical Properties

• Melting Point: 84-85°C
• Boiling Point: 433.3°Cat760mmHg
• Flash Point: 215.9°C
• Appearance: /
• Density: 0.879g/cm³
• Storage Temp.: -20°C Freezer
• CAS DataBase Reference: (E)-9-octadecenamide(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-9-octadecenamide(4303-70-2)
• EPA Substance Registry System: (E)-9-octadecenamide(4303-70-2)

Safety Data

• Hazardous Substances Data: 4303-70-2(Hazardous Substances Data)

Usage

Description

(E)-9-Octadecenamide, also known as Elaidamide, is a fatty acid amide that has been identified in the cerebrospinal fluid of sleep-deprived cats. It is a white solid and acts as a structural analog of oleamide, a sleep-inducing fatty acid amide naturally found in cerebrospinal fluid. Elaidamide exhibits inhibitory effects on rat microsomal epoxide hydrolase (mEH) and phospholipase A2 (PLA2) enzymes. It has been shown to induce physiological sleep in rats when administered in vivo.

Uses

Used in Pharmaceutical Industry:
(E)-9-Octadecenamide is used as a sleep-inducing agent for its ability to promote physiological sleep in rats. Its sleep-inducing properties make it a potential candidate for the development of therapeutics aimed at treating sleep disorders and improving sleep quality.
Used in Enzyme Inhibition:
(E)-9-Octadecenamide is used as an inhibitor of rat microsomal epoxide hydrolase (mEH) and phospholipase A2 (PLA2) enzymes. Its inhibitory effects on these enzymes can be leveraged in the development of drugs targeting various diseases and conditions where these enzymes play a role.
Used in Research and Development:
(E)-9-Octadecenamide serves as a valuable compound for research purposes, particularly in the study of sleep mechanisms, enzyme inhibition, and the development of novel therapeutics. Its unique properties and interactions with biological systems make it an important tool for scientific investigations in various fields, including neuroscience, pharmacology, and biochemistry.

InChI:InChI=1/C18H35NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H2,19,20)/b10-9+

Upstream product

• 55726-25-5 elaidic acid-anhydride 
• 112-77-6 elaidoyl chloride 
• 79-37-8 oxalyl dichloride 
• 112-79-8 Elaidic acid 
• 77287-34-4 formamide 
• 112-77-6 (Z)-9-octadecenoyl chloride 
• 537-39-3 trielaidin 

Downstream Products

• 112-90-3 oleylamine 
• 112-90-3 trans-oleylamine 
• 116749-36-1 trans-8-heptadecenylammonium tosylate 

Relevant articles and documents

Electrospray ionization and collision induced dissociation mass spectrometry of primary fatty acid amides

Primary fatty acid amides are a group of bioactive lipids that have been linked with a variety of biological processes such as sleep regulation and modulation of monoaminergic systems. As novel forms of these molecules continue to be discovered, more emphasis will be placed on selective, trace detection. Currently, there is no published experimental determination of collision induced dissociation of PFAMs. A select group of PFAM standards, 12 to 22 length carbon chains, were directly infused into an electrospray ionization source Quadrupole Time of Flight Mass Spectrometer. All standards were monitored in positive mode using the [M + H]+ peak. Mass Hunter Qualitative Analysis software was used to calculate empirical formulas of the product ions. All PFAMs showed losses of 14 m/z indicative of an acyl chain, while the monounsaturated group displayed neutral losses corresponding to H2O and NH3. The resulting spectra were used to propose fragmentation mechanisms. Isotopically labeled PFAMs were used to validate the proposed mechanisms. Patterns of saturated versus unsaturated standards were distinctive, allowing for simple differentiation. This determination will allow for fast, qualitative identification of PFAMs. Additionally, it will provide a method development tool for selection of unique product ions when analyzed in multiple reaction monitoring mode.

Fatty-acid amide hydrolase

The soporific activity of cis-9,10-octadecenoamide and other soporific fatty acid primary amides is neutralized by hydrolysis in the presence of fatty-acid amide hydrolase (FAAH). Hydrolysis of cis-9,10-octadecenoamide by FAAH leads to the formation of oleic acid, a compound without soporific activity. FAAH has be isolated and the gene encoding FAAH has been cloned, sequenced, and used to express recombinant FAAH. Inhibitors of FAAH are disclosed to block the hydrolase activity.

Method for sleep induction

Sleep may be induced by administration of fatty acid primary amides, including cis-9,10-octadecenoamide. Furthermore, sleep deprivation may be assayed by analyzing cerebrospinal fluid with respect to the presence of fatty acid primary amides, including cis-9,10-octadecenoamide. The presence of cis-9,10-octadecenoamide in cerebrospinal fluid is correlated with comparative sleep deprivation.